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Detroit’s unlikely downtown champion is from Richmond Hill

Detroit is teetering near bankruptcy but a Toronto investor is betting on its future with the purchase of landmark Penobscot Building, the old Silverdome and a plan for a string of casinos across the state.

Detroit is teetering near bankruptcy and suffering through decades of damage. But Andrea Apostolopoulos, the new owner of the Penobscot building in downtown Detroit, is trying to change that, one investment at a time. He's one a slate of entrepreneurs, investors and visionaries who believe Detroit has hit bottom and can only go up. (LUCAS OLENIUK / TORONTO STAR) | Order this photo

DETROIT—Andreas Apostolopoulos has only been in a casino once in his life. It was the quickest route to the underground parking lot.

But he’s gambling big time that this battered city has finally hit bottom.

Even as Detroit was teetering on the brink of bankruptcy this week, the 60-year-old Toronto-based investor was part of a consortium negotiating to open eight new casinos in this hard-hit state. He also added two more downtown highrises to the bargain he snapped up a week ago, the art deco Penobscot Building.

For just $4.8 million U.S. cash — just $4 per square foot — Apostolopoulos bought the smaller, 1928 equivalent of Toronto’s landmark Scotia Plaza tower which recently sold for $1.2 billion, or $600 per square foot.

“Detroit’s gonna be coming up again. I think it will switch around,” says Apostolopoulos, one of the most low-key investors — and there’s a spate of them — now making their mark on Detroit’s skyline.

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“I think the city is already bankrupt. I don’t think it could get any worse than it is.”

Three years ago Apostolopoulos’ Triple Properties Group paid just $583,000 — sight unseen — for the long-defunct Pontiac Silverdome, once described as “the world’s biggest fixer-upper.”

Today, as the soft-spoken, self-made multi-millionaire stands at one of Detroit’s biggest intersections, even he is caught off-guard by the scale of his latest trophy.

“I never looked at it from the outside like this,” says Apostolopoulos, transfixed by the cluster of three half-empty limestone office towers peaking at 47 storeys. “Now that I look at it from here, it looks better than I thought. It looks beautiful.”

Apostolopoulos is among hundreds of folks who are getting their hands very dirty trying to clean up this rust belt relic which is undergoing a development boom and entrepreneurial explosion.

Admittedly, Apostolopoulos is at least two decades older than most in the tight-knit group slowly turning Detroit’s lights back on: For decades, more than a quarter of its downtown office space sat empty. More than half the street lights still don’t work.

But there are hopeful signs thanks to a spirited, co-ordinated, grassroots effort by deep-pocketed philanthropic foundations, businesses and visionaries. Adding to it all are artists and a mass of newcomers to the city who want to make a living and a difference by growing a new generation of jobs, and neighbourhoods, in the shadow of the auto industry.

The majority are under the age of 40 and drawn here by the raw appeal of a once-mighty city that feels like East Berlin after the fall of the wall — facing huge challenges, but full of possibilities.

More than 5 million square feet of office space, most of it in grand old skyscrapers built during Detroit’s heydays in the early 20th century, are being renovated or converted to apartments, hotels and stores.

More than 350,000 square feet of new retail and restaurants is planned for the core which hasn’t had a shopping district for years.

The downtown workforce has grown by more than 8,000 people in the last two years alone.

Leading the revolution is native son Dan Gilbert, owner of Quicken Loans, who has bought up 2.5 million square feet of office space downtown and moved in some 4,000 employees, with 1,000 more to come.

That’s on the heels of other major corporate moves downtown, and incentives from nine major employers to bring Detroit back: Workers get $20,000 if they buy a home, $2,500 if they rent. That’s added more than 500 folks to the streets of downtown and up-and-coming Midtown, says Bob Gregory, senior vice president of Detroit Investment Fund.

“Everybody is nervous because of the image of Detroit. But we are finding once (potential investors) get here and talk to us, those fears go away. The (near) bankruptcy doesn’t help, but we all believe the political leadership will work through that.”

The bigger problem is jobs, and finding a fix for blighted neighbourhoods surrounding the core where huge swathes of homes — abandoned as folks turned elsewhere to live or work — remain burned out or stripped of anything valuable, including the posts that once held up porch roofs.

“Detroit still needs jobs. That’s the major challenge. And there are tremendous challenges in those neighbourhoods,” says Gregory. “But the thinking is that if you start with the core, that will have a ripple effect.”

Apostolopoulos is unlike most of the well-educated others who are snapping up cheap real estate.

He quit school in his native Greece after Grade 5 to help support his family: “I’m very good at math. On my school books there were times tables. I thought, ‘That’s all I need to know.’”

He and his three grown sons now oversee a collection of industrial and commercial buildings in Toronto, California and Australia.

He cut a vacation short to bid for the Silverdome, which had been shuttered for eight years, when one of his sons spotted an auction ad in The Toronto Star in 2009. The family had talked about owning a stadium and soccer team someday.

For $583,000 Apostolopoulos got an 82,000-seat stadium that had been constructed in 1975 for $55.7 million — about $220 million in 2009 dollars. He’s brought it back to life with concerts, monster truck competitions and $10 million in improvements. He’s still working at getting a team.

Since the Silverdome, Apostolopoulos has been spending three or four days a week in his adopted city. Three years ago, downtown streets were empty when Detroit — already reeling from decades of questionable urban planning, auto-industry downsizing and suffocation by the booming suburbs — was knocked on its back by the recession.

Today, as he stands outside the Penobscot, marvelling at all the people, Apostolopoulos looks content, even as a passerby pleads for money. “Here, my friend,” says Apostolopoulos, handing over $5.

“Everything is up and up and up. It’s not only to make money,” he says of the Penobscot purchase. “When opportunity comes, you have to grab it.

“I’m not going to be able myself to bring Detroit back. But if there are 20 or 30 people like me, buying (buildings) and bringing business here, it’s better than nothing.”

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